0.0 Start in downtown Orinda, just like you were doing the Bears Loop . Head South on San Pablo Dam Road, go under Highway 24 and stay on San Pablo Dam/Moraga Highway.
5.3 Turn right onto Canyon Road/Moraga Road. (If you turn left it's Moraga Road, if you turn right it's Canyon Road.) After heading out of town, the road will narrow and you'll start climbing a little.
7.1 Turn right onto Pinehurst Road. Here is where you'll really start to feel like you're out in the middle of nowhere. Traffic on this stretch is almost nonexistant. Notice what looks like a one room school house on the right side of the road in the town of Canyon.
After about two miles on Pinehurst you'll come to a left hand switchback turn. This is where the climbing begins. The climbing isn't terribly steep until the last half mile or so. The steeper section starts right after a sharp right switch back turn about half way up the climb. The road is pretty protected from the sun, for those hot summer days.
11.1 At the top, you go "kind of straight" onto Skyline Blvd. It's a five way intersection. Don't take a hard right, or either of the two options on your left. This is where you'll start to get some really spectacular views. Except for fires, obscene house payments, no flat yard to speak of, and maybe having your house slide down the hill, this is probably a spectacular place to live.
12.8 Turn right on Grizzly Peak Road. I always know it's about time to turn when I see the Robert Sibley Volcanic Regional Preserve. If you start going down and it looks like you're heading back to civilization, STOP!! You missed the turn. I know this from experience.
15.2 After a short descent you'll come to a four way intersection with a stop sign. Go straight through the intersection. If you turn left on Claremont Ave. you will end up in Berkeley. If you turn right on Fish Ranch Road, you will end up at Highway 24 with only two choices. Climb the hill you just went down or ride on the freeway to Orinda. Riding on the freeway here is legal if you need to make the ride shorter, but it's not that much fun. Once again, I know this from experience.
16.6 Just after you pass the Miniature train at Tilden Park, turn right on South Park Drive. This is the beginning of a very steep descent. Be careful! You could easily reach speeds of over 50mph here. That's not necessarily a problem, but dealing with other park users not looking for bikes coming down the hill at 50mph would be! About half way down on the left is a bathroom if you should feel the need.
18.1 Turn right onto Wildcat Canyon Road when you get to the stop sign at the bottom.
19.3 On the left is Inspiration Point. Isn't that where they used to go and make out on Happy Days? Anyway, the descent of Wildcat Canyon begins here. It's a little twisty so keep on your toes.
21.7 Turn right on San Pablo Dam Road and head back towards Orinda. Unless you want to turn left and ride a lap or two on the Bears Loop.
